


The Office Headcanons

by snagglepuss



Category: The Office (US)
Genre: F/M, Fluff
Language: English
Status: In-Progress
Published: 2019-05-27
Updated: 2019-11-22
Packaged: 2020-03-19 23:55:03
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 17
Words: 8,976
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18980959
Author URL: https://archiveofourown.org/users/snagglepuss/pseuds/snagglepuss
Summary: The title says it all, my friends.





	1. Meeting

**Author's Note:**

> Helloooo again :) There are very very few reader-insert headcanons for this show and I deem that a great injustice, so here ya go. I make no promises that they’re good or accurate, but I hope you like ‘em anyway.

**Dwight Schrute**

-Super rude

-Quickly picks up that you kinda suck at sales

-Refuses to help you because true salesmen are GIFTED not TAUGHT

-You slowly bond over your love for battlestar galactica 

 

**Michael Scott**  


- _‘Oh, hello. I thought we hired an accountant, not Eva Longoria’s long lost TWIN’_

-You look NOTHING like Eva Longoria but it’s okay because of the way he looks at you when he says it

- _‘We have the same birthday you know’_

- _‘Hey, do you have a picture of your mom? I bet she’s a total babe’_

**Jim Halpert**

-Just smirks at you

-He keeps glancing at your desk next to his

-Every time he looks you get all tingly but you pretend like you don’t know he’s watching

-Offers to buy you a bag of chips

 

**Ryan Howard**

-Kinda awkward but also kinda smooth

-A lil cocky but in a cutesie way

-Flexes his business skills to try and impress you

-You quickly find out his nickname is ‘fire guy’ but he lets you call him it because you’re cute

 

**Toby Flenderson**

-SO SWEET AND SHY

-Only person to go out of their way to be nice to you (except maybe Pam because she’s, y’know, an angel)

- _‘h-hey.. if you need anything, let me know. i’ll be... here if you want to talk or.. something’_

-He stares at the floor when he talks to you and you can tell he’s nervous as heck

 

**Gabe Lewis**

-Super painfully awkward

-Tries to show how powerful he is in the office

-Fails

-Goes and pouts somewhere but you don’t mind because at least he tried to impress you

 

**Andy Bernard**

-Desperately tries to open every door for you

- _‘Hey, what college did you go to?’_

-Talks about Cornell pretty much the entire time

-You just pay attention to the way his eyes light up because he loves it so much

-Immediately tries to woo you shamelessly


	2. When They Fall For You

**Dwight Schrute**

-He takes you on a sales call

-Not because he wants to but because Michael makes him

-You rev up with him in the car by listening to heavy metal

-You end up convincing the company to buy a heck of a lot of paper

-Dwight gets so excited he forgets that he hates you

-He smiles at you (sorta. you know Dwight and his sly looks) when you fall asleep in the car

 

**Michael Scott**

-He tells you about Threat Level Midnight

-You offer to read the script for him

-He immediately lights up and makes Pam print three copies in case you lose the first two

-It isn’t very good but you think his enthusiasm is adorable so you tell him it’s the best thing you’ve ever read 

-He offers you a part as one of Michael Scarn’s secret and illustrious lovers

 

**Jim Halpert**

-You’re bored so you decide to send Dwight emails from the president 

-Jim catches wind of this and you let him read them over your shoulder

-You giggle together over Dwight’s reaction because he’s gullible

-He decides to include you on his pranks from now on

-You try to buy a grape soda but the machine’s out so he offers his to you

 

**Ryan Howard**

-You offer to go with him to find fresh yams for Michael when he cooks his foot

-You admire how clean his car is 

-He lets you listen to whatever you want

-He gets so distracted by your presence in his car that he misses a few turns and ends up in Carbondale

-It’s okay though because at least he’s with you 

-You find the pudding cups Michael mentioned at a gas station nearby

-He asks you if you want to stop for coffee as a ‘thank you’ for helping him but you both know it’s because he likes you

 

**Toby Flenderson**

-You meet his daughter on take your daughter to work day

-You fall in love with her because shes so SWEET just like her DAD

-She sees you reading Harry Potter on your break and asks you to read it to her

-He watches you read from afar with the cutest twinkle in his eye

-He laughs at your Hagrid impression

-Realizes you would be an adorable mom

 

**Gabe Lewis**

-He watches you all day

-Every day

-I don’t even know what to say he just thinks you’re an angel

-Barely talks to you though because every time he does he gets embarrassed

 

**Andy Bernard**

-He constantly talks to you about all the things he likes

-He tells you about his time in Here Comes Treble

-You love music (or do you just love him?) so you spend all of your breaks for three days watching performances on his laptop

-He loves your commentary and wonders what it would be like to sing with you


	3. When They Ask You Out

**Dwight Schrute**

-Demands you come to his beet farm to ‘discuss sales’

-He really just wants to have a picnic with you on his dusty barn floor

-He gets *secretly* excited when you actually agree to eat his beets

 

**Michael Scott**

- _‘Hey, so it turns out corporate is demanding all beautiful female employees go to lunch with the manager and since you’re the only one here..’_

- _‘Except pam, but she doesn’t count.’_

-You try to talk but he doesn’t let you

- _‘I’m serious. do it or you’re fired.’_

- _‘Just kidding. but no.. seriously, I will fire you.’_

  

**Jim Halpert**

-Super casual about it

-Doesn’t even really ask but you don’t mind

- _‘So hey, I may or may not have a coupon for that new Chinese place across town, so I figured I’d pick you up at like 7’_

 

**Ryan Howard**

-Signature awkward but smooth convo

-You’re both at lunch and he just kind of brings it up

-Asks you about some weird bar you’ve never been to but you pretend like you’ve been there because he has

- _‘Oh. Cool. So, do you think I’ll see you there tonight?’_

 

**Toby Flenderson**

-He doesn’t. 

-He approaches you but walks away like five times in an hour

-You eventually get fed up and visit him in the annex

-He gets so glowy and flattered when he sees you went out of your way to come see him

- _‘hiiiii, y/n.’_

-He blushes just saying hello

-You tell him that you really love his daughter but suggest that maybe possibly you should hang out without her so you can ‘get to know him better’

-He is literally so happy that he radiates for the rest of the day

 

**Gabe Lewis**

-Watches you enter the kitchen from across the office

-Kinda invades your personal space but you don’t mind that much

- _‘Did you want to.. uh.. go to.. dinner with me? I thought maybe if you weren’t busy and since I’m not busy and since it’s friday so... yeah, you’re probably busy so I’ll just leave okay bye.’_

-You end up having to stop him before he runs away to tell him you’d love to

-Awkwardly mumbles a goodbye before going back to pretending he’s the shit

 

**Andy Bernard**

-Just kind of shows up at your apartment

-He’s carrying a puppy because he’s Andy and of course he’d do something like that 

- _‘Hey! So, I saw this little guy at the pet store and I couldn’t help but think of you’_

_-‘You know... because he’s cute.’_

-He insists you keep it but you tell him you don’t want him to spend a bunch of money on you

- _‘Well, too late, I guess because I already bought these.’_

-Whips out tickets to some broadway musical in new york


	4. The First Date

**Dwight Schrute**

-You’re greeted by Mose as soon as you get there

-He insists he parks your car

-You know you shouldn’t let him but you don’t know what to say

-Dwight walks out on the porch wearing a flannel

-It looks like he actually tried a little

-That makes you go aww

-He spends the night cooking for you and feeding you little spoonfuls of his beet dishes

-They’re surprisingly good?

-You end the night on his couch having a debate about Lord of the Rings before your car shows back up

  

**Michael Scott**

-He surprisingly doesn’t take you to Hooters

-That makes you happy

-He takes you to a nice seafood place but insists you order the chicken fingers 

-You do it just to make him happy

-He makes jokes the whole time (purposely leaves out the raunchy ones) and even reaches across the table to hold your hand

-awwwwwwwwwwwwww

-‘til he tries to kiss you

  

**Jim Halpert**

-You get Chinese at this really tiny place and sit at one of the booths

-You end up talking about movies and he does his best impressions 

-They’re awful and he knows that but they still make you laugh

-You both decide you’d rather just watch the movies

-You spend the rest of the night making fun of bad movies at Jim’s apartment

  

**Ryan Howard**

-You look really good

-Like really good

-And Ryan notices

-He sees you walking toward the bar but he pretends like he didn’t so he can go ‘ _Oh, hey! Didn’t see you there_!’

-When he does ‘see’ you he immediately offers to buy you whatever you want even though he’s dead broke bro

-You just kinda talk the whole night until he shyly invites you back to his apartment

  

**Toby Flenderson**

-He’s driving, but every time you ask where you’re going he just smiles and mumbles ‘ _It’s a surprise_ ’

-You keep trying to get him to tell you and you even debate kissing that cute lil smile off of his face

-You eventually tell him this but he just blushesand looks at you like he can’t believe someone would actually want to kiss him

-But you really DO want to 

-Turns out he’s taking you to the lake

-You both spend the whole time looking out at the water and talking about everything that makes him happy, like his book and his daughter

 

**Gabe Lewis**

-You somehow convince him to go ice skating

-He’s so TALL and so unbalanced 

-But he reaches out to hold your hand when he’s about to fall and that makes you go aw

-It’s kinda awkward having to stop such a tall guy from falling

-But you don’t mind because he’s so CUTE when he looks at you like he needs your help

 

**Andy Bernard**

-You spend the whole drive to new york singing soundtracks to a ton of movies

-He even sings ‘My Heart Will Go On’ with you

-You swear he was going to kiss you during the last chorus

-But he doesn’t because the narddog is a gentleman and must try not to give non-consensual kisses

-You both think the show is amazing and have a deep and intelligent convo about it on the way home

-He desperately just wants you to crash on his couch so he can see you as soon as he wakes up but he takes you home because he wants you to be comfortable


	5. Your First Kiss

**Summary for the Chapter:**

> Kisses from the sweet boys <3

**Dwight Schrute**

-You’re the last two people in the office at the end of the day

-He offers to walk you to your car

-‘ _Oh, look! The elevator seems to be malfunctioning! I guess we have to take the stairs!_ ’

-The elevator is working fine but you go with him anyway

-You’re in the middle of the stairwell telling him about your weekend plans when he grabs your face and tells you to shut up

-He just kind of smashes your faces together at first until you help him chill out

 

**Michael Scott**

-Calls you into his office for an ‘urgent meeting’

-He tries to fake fire you like he did with Pam

-Rearranges his desk toys to avoid making eye contact with you

-When he sees the joke actually makes you upset he feels like he just destroyed all things good in the world

-He’s immediately kneeling at your side

-‘ _Oh no no no, are you crying? It was a joke! Laugh. Please Laugh. Please._ ’

-He takes your face in his hands because you’re still not laughing and just kisses you because he doesn’t know what else to do

-When he pulls away he whispers, ‘ _you’ve been exe’d, punk_.’

 

**Jim Halpert**

-He drives you home after your first date

-It’s kinda the cliché thing where he walks you to the door like the chivalrous gentleman he is

-‘ _I had a really, really nice time tonight_.’

-He starts to act kind of shy and rubs the back of his neck while you just smile

-He can’t decide if he should ask to kiss you or wait until next time, if you agree to a next time

-You decide for him when you reach up and kiss the lanky ole’ fool

-When you pull away he just chuckles breathlessly and asks

-‘ _Can I see you again?_ ’

 

**Ryan Howard**

-At first you’re skeptical about going back to Ryan’s apartment

-But then you decide you don’t care because you’re cute and he’s cute and why not

-When you get there he’s actually not all over you like you thought he’d be but he’s actually kind of shy

-‘ _You know... I was gonna ask if you wanted to stay, but then I realized you’d probably think I was just using you and I don’t want you to think that you’re just a quick fuck or something because you’re not, like... at all, and I actually really, really like you so if you want to watch a movie or something, I’d really like that_ ’

-‘ _Not that I don’t want to sleep with you because I mean look at you, you’re beautiful. But I don’t want to push you into something you’re not ready for so I’ll go make some popcorn. You want some?_ ’

-You can’t stop smiling because he’s rambling and you just didn’t expect this so yeah, you kiss him because what other choice do you have? 

-It’s all warm and sweet and his fingers are shaking when they squeeze your waist 

**Toby Flenderson**

-He’s way too shy to make the first move but you don’t mind

-You know it’s been awhile since he’s kissed anyone so you don’t want to push

-But when you’re telling him about your favorite memories and he just looks at you like he can’t believe you’re even talking to him HOW CAN YOU HELP YOURSELF

-You stop mid sentence and kiss him with all the love and adoration that sweet boy desperately deserves but never got

-He’s so nervous and the soft whimper he makes when you kiss him harder just makes your heart ache thinking about how long he’s spent feeling like no one wants him

  

**Gabe Lewis**

-He walks you to your car after the first date

-You can tell he wants to kiss you but he’s still thinking about it

-You’re patient and let him work up the courage to kiss you because you know how important it is to him to feel like he can take care of you

-When he finally does kiss you it’s kind of an awkward mess but you slowly try to help him out

-He doesn’t have much experience but he is very, very eager to learn and he follows your lead in the long, sweet kiss you share

 

**Andy Bernard**

-You come to see his show

-When he sees you after he literally gets so adorably excited that it makes you all warm inside

-‘ _Y/n! you came!_ ’

-You just smile at him because OF COURSE you came, silly Andy

-You tell him you thought he was better than any of the actors you’d seen on broadway (and you genuinely kinda think so)

-He knows you’re just being nice but he thinks it’s sweet so he can’t help but kiss you until you both can’t breathe like they do in the movies


	6. How They Cuddle

**Dwight Schrute**

-He kinda spoons you but keeps an iron grip on you the whole time

-It’s like he’s scared you’re going to run away

-But you’d never because he actually really does make you feel safe

 

**Michael Scott**

-Space? What is space?

-He practically climbs on top of you

-You think it might just be his way of keeping you from sneaking out at night

-You would get annoyed by it but he kisses your face every five minutes and somehow the cuteness of that just makes it worth it

  

**Jim Halpert**

-He loves casual cuddling

-Basically cool with any type at any time

-Most of the time you just end up with your head on his chest while he fiddles with your hair and gives you that goofy smile in the dark

  

**Ryan Howard**

-He swears he doesn’t really like to cuddle

-But he can’t stop himself from doing it anyway

-So you just kind of end up with his arm across your body at various points at night

-You kinda wish he’d cuddle with you and he knows that so he doesn’t stop you when you come closer

  

**Tob y Flenderson**

-You can feel how content he is whenever he pulls you close to him

-He’s just glad he doesn’t have to sleep alone anymore honestly 

-He’s shy but also eager because he genuinely does like you

-He just hasn’t been with anyone for so long

-You sometimes feel him reach out for you gently and then pull away, like he’s just checking to make sure you haven’t disappeared 

 

**Gabe Lewis**

-He’s still so shy

-He loves to cuddle but he won’t unless you initiate it

-He never really knows what to do with his hands and he doesn’t want to make you uncomfortable so you kind of have to guide him

-You think the shyness is cute but you also wish he knew how much you liked him and wasn’t so afraid to touch you

-He’s in awe whenever you let him hold you and he sneaks super innocent kisses to your face when he feels confident enough

 

**Andy Bernard**

-He LOVES being close to you and probably likes cuddling even more than you do

-He doesn’t even care how close you are as long as you’re comfortable 

-But his favorite way to cuddle is with your body pressed fully against his with your face in his chest and your legs intertwined

-Honestly he would just let you sleep directly on top of him if he could


	7. Cute Things They Do

**Dwight Schrute**

-He gets really protective over you

-Like if he thinks the wrong person is breathing in your direction he will go full Jackie Chan on their ass until you have to tell him to calm down

-He just wants you to feel safe

 

**Michael Scott**

-Everyone knows Michael has a diary

-You don’t want to invade his privacy

-You really, really don’t 

-But one night he just leaves it open and it’s like he wants you to find it 

-So you just take a quick peek and wow you’re so glad you did

-You find a super long ramble about you

-It’s basically just a long list of all the things he wants to do with you and how much he thinks you have a future together

-You don’t know but he ALWAYS writes about you

-He wants to tell the world about you and he would shout his love for you from the top of the office building if you’d let him but for now he just writes it in his diary

  

**Jim Halpert**

-Okay everyone knows Jim is the cutest boy who goes out of his way with all the romantic gestures

-But you didn’t realize just how much effort he put into them

-Since you’ve been dating he’s started working EXTRA hard so he has enough money to treat you to nice things

-He really, really wants you to know how much he likes you

-So he makes excuses to give you little gifts like meaningful trinkets and flowers

-And he insists on taking you on nice but casual dates as often as he can

-He’s a stickler about making time for you and ensuring you’re happy with him and you are, how could you not be?

  

**Ryan Howard**

-Baby boy has a HUGE ego

-It’s not surprising that his favorite thing ever is to show you off

-Wherever you go, he wants to have his arm around you and introduce you as his because you are and he’s damn proud of that

-Sometimes it’s annoying and you feel like you have to reassure him that yes, you’re proud to be with him but he doesn’t have to tell everyone for that to be true

-But he gets this face whenever he introduces you to someone new like he’s just so excited to have someone as cute and wonderful as you

 

**Toby Flenderson**

-He’s a great dad, even if he doesn’t get to see Sasha much since the divorce

-A lot of that cute protective behavior gets carried into his relationship with you

-Like him making you dinner, making sure you get enough sleep, even giving you vitamins he thinks you should take to keep from getting sick

-All the little things he does for Sasha he ends up doing for you 

-But not in a weird way

-It lets you know he cares about you enough to want to keep you safe and healthy

 

**Gabe Lewis**

-Okay so we know this guy is very boastful yet fragile

-He’s basically the perfect example of ‘all bark, no bite’

-That would definitely play a big part in your relationship 

-He would talk so much shit about how he could hurt anyone that ever came near you

-Kind of like Dwight, but Dwight would legitimately hurt people, not Gabe

-You know he’s all talk but it’s sweet how much he wants you to think he’s big and strong so you go with it

-Like I said, it makes him feel good to know he can take care of you and in a lot of ways, he can, so you just humor him on this one

  

**Andy Bernard**

-He loves to sneak up on you and give you those cute little hugs from behind 

-And then he hums softly in your ear while you both sway back and forth and he kisses the side of your face over and over

-He also loves to sing you to sleep and you love that he goes out of his way to sing your favorite songs


	8. How They Take Care Of You When You’re Sick

** Dwight Schrute **

-He won’t

-He just tells you that if you listened and followed the diet plan he set out for you, this never would have happened

-The most he’ll do is toss a box of tissues at you when he shows up at your doorstep wearing a mask and disposable gloves

**Michael Scott**

-He BABIES you because he knows that’s how he’d like to be treated

-He would totally take great care of you

-Michael can’t cook but he would absolutely stop to pick something up for you

-He gets you the softest tissues and waits on you hand and foot

-He’ll hold you the whole time or offer to give you a massage because he doesn’t care if he gets sick, he just wants you to feel better

 

**Jim Halpert**

-He won’t hound you. He knows when you need your space

-that being said, he still makes sure to take care of you

-He’ll get you medicine and try to make you soup, but it might just end up coming from a can

-If you ask him to he’ll cuddle with you and watch whatever you want 

 

 

**Ryan Howard**

-Like I said, he’s not good with physical affection

-He also hates getting sick because catching up on business school is a bitch

-Still, he’ll try to pick something up for you if you ask for it

-He’ll send you a few texts throughout the day like

- _you feeling okay?_ and

- _do you want me to stop by?_

 

**Toby Flenderson**

-He’s a dad so, A+ care when you’re feelin under the weather

-He’ll do basic stuff, like bringing you water bottles, advil and extra blankets

-If you’re really sick, he won’t shy away from it

-He’ll hold your hair back for you while you throw up and clean up after you if you need it

-He makes sure you eat and get your vitamins

-If you want him to, he’ll draw you a bath or bring you a spare set of clothes

 

**Gabe Lewis**

-He’s a bit of a germaphobe but he wants you to feel better

-He has no clue what you need so he freaks and buys whatever the pharmacist says might help

-He wants to take care of you but he really doesn’t want to get sick

-but if you ask him nicely he’ll try for you

 

**Andy Bernard**

-He goes all out

-Buying you all the top of the line medicine available even if you tell him not to

-But it doesn’t stop there

-I’m talking hardcore vitamins, hot water bottles, heated blankets, popsicles, literally ANYTHING you could possibly need

-and a lil bit of narddog serenading on top


	9. PDA

**Dwight Schrute**

-The only time he initiates PDA is when he thinks he has something to prove

-If Jim has put him through a lot of teasing he might kiss you just to remind everyone that he scored such a cutie pie

-But overall, Dwight likes to keep stuff like that private

 

**Michael Scott**

-Okay. We already know.

-Michael Scott=PDA KING

-He constantly makes up excuses to swing by your desk and kiss you

-holds your hand whenever he possibly can

-He loves touching you because he spent so long with no one who would let him so, he feels like he has to make up for lost time

 

**Jim Halpert**

-Classy, classy Big Tuna

-He’s not afraid to hold your hand every once in awhile or give you a casual kiss in passing

-But for the most part he keeps it clean

-He’d love to touch you, believe me, but he knows some things just shouldn’t be on full display

 

**Ryan Howard**

-He loves PDA purely because he wants everyone to know about you

-He loves introducing you to people or keeping his arm around you so they know right away who he’s with

-Sometimes he’ll take it a little far but he really has no shame in his affection for you, though he’ll occasionally struggle when it comes to doing it genuinely, behind closed doors

 

**Toby Flenderson**

-He loves PDA and the feeling of you maybe possibly being proud to be with him but he never initiates it

-He doesn’t want to embarrass you or push you

-If you do touch him he gets all flustered and happy and it’s just a SIGHT to see, my friend

 

**Gabe Lewis**

-he wants to touch

-he really really wants to touch

-and sometimes he will

-but then he gets clumsy and does something wrong or awkward

-and then he’s embarrassed for the rest of the day until you come by to make him feel better

 

**Andrew Bernard**

-Andy is a sweet boy

-a very sweet boy

-He loves little kisses and hugs and hand holding and all that good stuff

-Whenever you need a lil piece o’ the narddog, he’s ready and willing


	10. When They See You Cry

**Dwight Schrute**   


-Dwight gets awkward because he’s not good with emotions

-He might not even ask what’s wrong, he’ll just go on an epic manhunt to destroy whoever made you upset

-Then, after work he takes you to his farm and you sit in his lap while you watch some sci-fi movie

 

**Michael Scott**   


-We already kinda went over the first time he sees you cry

-But every time he sees you cry after that he just makes jokes until you laugh and then he gives you the biggest hug

 

**Jim Halpert**

-Super caring boyfriend

-He knows when you’re upset basically immediately because he’s always watching out for you

-When he sees you he’ll take you out somewhere private and give you a hug

-He’ll make sure you’re okay and then give you some space and a tissue

-While you’re recollecting yourself he gets you some water and then IMs you stuff about Dwight to make you feel better

 

**Ryan Howard**

-The one time Ryan will offer to hold you

-He struggles when it comes to communicating with you but he gets really scared you’re crying because of him so when he offers to help he’s really careful about it

-Sometimes he’ll just start apologizing and reach out for you because he’s so used to screwing things up

 

**Toby Flenderson**

-Once again, he’s a great dad of a cute kid

-When you cry he gets so sad for you

-He’ll push your hair out of your face and wipe your tears and talk you through everything

-He wants to make you laugh or kiss you or something so you’ll stop crying but he’s never been good at that sort of thing

-So he just gets you tissues and whispers ‘ _hey, shhhhh, it’s okay_ ’ a lot

 

**Gabe Lewis**

-Again, awkward

-But he knows immediately when you’re sad because he’s literally always watching you

-He offers to fire whoever made you cry even though he doesn’t have that kind of power

-He wants to help but he doesn’t. know. how. and it frustrates him to no end

 

**Andy Bernard**

-He’ll take you wherever you want and hold your hand the whole time

-Heck, he’ll take you to disney world then and there if it’ll make you feel better

-He LOVES you and ‘ _nobody messes with the Narddog’s lady_ ’

-Whatever you need, he’s got you

-But if you ask him for space he gets a little hurt just because he wants to be near you


	11. Meeting Their Friends

**Dwight Schrute**

-You already know this is going to be a rollercoaster 

-His friends are so weird but he really wants you to like them

-So you pretend like you do even if you don’t

-Some of them aren’t even that bad when you get to know them

-But he’s very protective around them because he doesn’t want them to steal you

 

**Michael Scott**

-Poor boy doesn’t have that many friends :(

-Besides Dwight and Todd Packer, you have most of his attention

-Speaking of Packer, if he ever says anything to you you don’t like, you just let Michael know and he talks to him about it

-Because you>anyone else

-Even Todd Packer

-You’re his world

-He literally loves you so much like I hope you understand Michael Scott would literally be the most attentive and loving boyfriend ever

 

**Jim Halpert**

-Of course you see his roommate all the time because Jim always invites you over

-But all of his friends are nice and polite

-They’d be super cool like him and he’d make sure you fit right in and never feel left out

 

**Ryan Howard**

-You’d meet his friends almost right away

-Some of them are kind of douches

-But he’s very happy around you and they’d notice that

-Having you there makes him come out of his shell a little more

-He likes to go out but he also likes to stay home and play video games so if you want to leave he will right away

 

**Toby Flenderson**

-Okay honestly this poor angel might not have many friends either 

-But the few he does have are very kind and supportive of your relationship

-They’re all mostly moms he met through Sasha and they’re just glad he’s happy because Sasha is happier now too

 

**Gabe Lewis**

-His friends are all dorky

-And socially awkward

-But you don’t mind

-He likes showing you off to them and it’s actually kind of sweet

 

**Andy Bernard**

-Meeting the legendary Broccoli Rob was a holiday for Andy

-He was so desperate for you to like all of his college friends like you have no idea

-He looooooves his friends and he’d make you put up with them a lot

-Like, volunteering you to drive them around and do whatever they want

-But you know it makes him happy so you just do it, even if his friends are annoying


	12. Nicknames

**Dwight Schrute**

-He calls you something weird around other people like your name backwards and in german or pig latin or some shit

-In private he has a whole list of names ranging from ‘beet mama’ to ‘female companion’ 

 

**Michael Scott**

-He has thankfully abandoned the term ‘babe’ after the Jan incident

-He likes to call you his ‘sugamama’ even though he makes more money than you 

-That ones mostly around other people

-In private Michael calls you ‘honey’ when he’s in one of his domestic moods

 

**Jim Halpert**

-His nicknames are very unique to you

-Like a play on your name or something from an inside joke

-If he’s feeling unoriginal he’ll just call you ‘love’ or something because it’s classy

 

**Ryan Howard**

-He seems like he throws around ‘baby’ and ‘babe’ a lot 

-Maybe even ‘babycakes’ if he’s in a playful mood

-Possibly even ‘cutie’ every once in awhile when he’s sleepy

 

**Toby Flenderson**

-He totally calls you ‘sweetheart’

-Sometimes ‘honey’ but i’m telling you you’re his sweetheart

 

**Gabe Lewis**

-He’d want to call you ‘baby’ just because it makes him feel grown up

-But the first time he says it it’ll just kind of slip out and he’ll be SO embarrassed

-Sometimes he’ll settle on a ‘sweetheart’ 

-But he really likes his first choice a lot more

 

**Andy Bernard**

-The real question is, what does this man not call you?

-‘Honey’ ‘sugar’ ‘dollface’ ‘babe’

-The whole nine yards

-He just calls you whatever he’s feeling that day

-His favorite thing to call you is ‘angel’ because ‘ _c’mon, thats what you are!_ ’


	13. Casual Nights In

**Dwight Schrute**  


-Every night is about as casual as it gets

-He tries but not in any normal way whatsoever

-Whenever you come over he feels the need to make a huge meal for you

-It’s not bad but he always wants to teach you how to kill the animals first so if that’s not couple goals

 

**Michael Scott**  


-Whenever Whose Line Is It Anyway is on you know he’s gotta make a holiday of it

-He invites you over and ‘cooks’ dinner

-Usually it’s just pizza rolls or a tv dinner or something

-But then you cuddle on the couch and you listen to him laugh all night

 

**Jim Halpert**

-He is the king of making casual nights still feel special

-Whether you order a pizza or just heat up leftovers it’s always cute and fun because he’s JIM

-He’ll still light a candle and make it look nice

-And then you’ll make a pillow fort or something because that’s just something he would do

-You watch whatever bad movies you can find until you fall asleep and he carries you up to his room

 

**Ryan Howard**

-Remember when he said he’d tell Danny Cordray he worked at Stark Industries?

-He’s a big Marvel dork

-Don’t fight me it’s true

-You guys have probably watched Fantastic Four a million times

-He even has a huge comic collection but shhhhh you can’t tell anyone

-So whenever you have a casual night in you watch a superhero movie and he talks to you about it til you fall asleep 

 

**Toby Flenderson**

-You usually have casual nights whenever he has Sasha

-He makes a nice dinner and then all three of you snuggle up on the couch to watch a new disney movie

-It’s not the most romantic thing but he appreciates so much that you love Sasha and understand that she comes first

-After he puts Sasha to bed he lets you watch whatever you want but secretly he just wants to kiss you the whole time because how did he get so lucky?

 

**Gabe Lewis**

-It’s gonna take a lot to convince him that casual nights are acceptable

-He always wants things to be perfect for you and he gets really frustrated when his plans fall through

-When you tell him you want him to come over just to watch a couple of movies or something he gets so confused

-What should he bring? Will he be sleeping over? Does this affair require a tie?? Give him some guidance because he is LOST

-He never feels like he’s enough for you so the fact that you’re content to just spend the entire night all warm and snuggled up against him means everything to him

 

**Andy Bernard**

-Nights in are the best with him because he always gets the absolute best snacks

-Like he goes out and buys everything he can think of that you like

-Dinner? He’s already ordered it

-Movies? He’s already picked out all of your favorites

-You always tell him he doesn’t have to go to so much trouble

-He just tells you to hush because you’re his lady and if he wants to spoil you he has that right


	14. When You Move In

**Notes for the Chapter:**

> Please leave requests man this writer’s block is brutal

**Dwight Schrute**

-Insists on moving all furniture by himself

-and he STRUGGLES

-but he won’t dare tell you that

-So you just watch him take a million trips in his old pick up because he REFUSES to get a moving van

 

**Michael Scott**

-He’s actually a lil apprehensive about it since what happened with Jan

-but his condo still gets lonely sometimes

-and he really wants to see your face every time he comes home

-So he finally asks you and OF COURSE you say yes why wouldn’t you

-Your first night in you eat ice cream on the floor like kids while the movers bring your stuff in

 

**Jim Halpert**

-We know he loves big surprises 

-So one night when you’re out of town he takes the opportunity to move all your stuff in

-The night you come home he makes dinner for you and goes all out 

-But on his way to the airport to pick you up he gets so SCARED that you’re gonna be mad at him

-and at first you kinda are

-until you see how nice he made the place look

-and that he made all of your favorites for dinner

-and he had this look in his eye when you didn’t smile right away that broke your heart

-so how COULD you be mad at him he is so sweet

 

**Ryan Howard**

-This was very hard for him

-He isn’t used to having people in his space

-But he can’t help how much he misses you when you’re away

-So... maybe his secret domestic side wins a lil bit

-Only because you’re so cute tho

 

**Toby Flenderson**

-He is still so used to having his family around that having you there wouldn’t really be that different for him

-But he is so bad at asking you

-and every time he tries he chokes up and pretends he never said anything

-Until you finally catch on to what he’s trying to say and tell him how much you’d LOVE to be with him every day

-You move in within a week

-and Toby has literally never been so happy

 

**Gabe Lewis**

-Gabe? Power moves? Sign him up. 

-Just kidding don’t

-He’s really awkward

-So instead of bringing it up to you he just hires the movers and they show up early on a saturday

-At first you’re like >:( but then you see how much it means to him

-and you think about how nice it would be to be around him all the time

-Maybe you’re a little soft for him anyway

 

**Andy Bernard**

-He buys a house for the two of you

-Kind of pulls a canon!Jim

-Except it’s not a surprise 

-Because his engagement to Angela made him so apprehensive about EVERY little detail and decision

-So at first he tries to keep it a secret

-But then he caves and tells you everything he’s been planning

-You meet with a realtor the next day and are really glad he didn’t keep it a secret

-because he’s Andy and OF COURSE it was too extravagant 

-And sometimes he needs to be reminded a little that it’s not about what he buys, it’s about being with him


	15. Thanksgiving

**Summary for the Chapter:**

> Something festive for all of you :) I hope you guys have a happy and safe holiday! <3

** Dwight Schrute **

-You already know he kills everything himself

-and if you tell him not to he will look at you with such disdain

- _Y/n, it’s important you learn these things in the inevitable event that i’m recruited by a secret government program, get my brain wiped and am forced to leave you forever!_

- _ ok Dwight. _

-Spending time with Dwight is actually fun when you get past the weird stuff

-as usual. 

-Mose is there too and BOY if he isn’t excited..

-After dinner they both tell you about their family’s traditions

-and you find out he actually left out some of his usual traditions just so he wouldn’t scare you away

-He is softer than he poses just take my word for it

-but after a lot of arguing he agrees that next year... you’ll just buy a turkey

 

**Michael Scott**

-He can’t cook

-and he doesn’t even try

-He offers to just make Dwight do it

-but instead, you just go to his mom’s

-which is quite the trip let me tell you

-Michael is a big mama’s boy

-and he definitely got his sense of humor from her

-So, naturally, dinner was chaos. 

-but she LOVES you

-and is so happy her boy finally found someone that loves him

-You have that touching moment where you guys really connect and bond over Michael’s endearing quirks even if he can be a lot sometimes

-Wholesome <3

 

** Jim Halpert **

-Jim’s definitely the type to go see his mama for thanksgiving

-and he’d LOVE to take you home with him to meet her

-but he doesn’t wanna rush you like that

-So instead, he plans his own little thanksgiving with you a few days before

-Jim seems like the type who can cook a little... so you tag team it. 

-You both do your best but it’s JIM of course he’s being distracting

-so if by the end of the night, you both are covered in more food than you’ve eaten, neither of you really mind. 

 

** Ryan Howard **

-Neither of you are really into conventionality

-and you’re both broke

-but Phyllis definitely offers some of her leftovers from the friendsgiving thing you have at work

-So it ends up a quiet evening eating whatever

-and hardcore snuggling... even if Ryan pretends he hates it

-He would literally do anything for you

 

** Toby Flenderson **

-He is literally so excited

-Getting to spend a holiday with both you and Sasha? Yes please. 

-He’s had lots of experience so, cooking won’t be a problem

-but he loves the way you and Sasha help

-He almost tears up when he thinks about how you guys are turning into a little family

-and he never thought he’d have a family again

-He’s never had a better holiday

 

** Gabe Lewis **

-His family lives far away

-So instead of bringing you home, you bring him home. 

-This boy has never been so nervous in his life

- _ Gabe, it’s gonna be okay. My mom’s nice.  _

- _Gabe, are you listening?_

- _Oh my god Gabe-breathe- you have to start BREATHING- oh my god GABE_

- It’s a struggle. and that’s just the drive. 

-He stutters when he introduces himself to your mom

-but you know he’s trying his best because he just really wants them to see how much he adores you

-and that’s more than you could ask for. 

 

** Andy Bernard **

-Of course, he brings you home. 

-The whole way there, he talks about how excited they’ll be to meet you

-He literally cannot wait the narddog is SO ready for this

-Until he gets there

-That’s when he sees the girl his brother brought home

-and his parents basically ignore him the moment he walks in

-He’s okay with it at first

-Until they brush  you  off

-THATS when he gets mad

-Long story short, you both end up eating takeout while you hold him on the couch and try to make him feel better about his parents being he worst

-He ‘s still sad but you make everything better so, he knows he’ll be okay.


	16. Christmas

**Notes for the Chapter:**

> Merry Christmas :)

** Dwight Schrute **

-Christmas at Schrute Farms is truly something else. 

-At first you’re a little horrified (and rightfully so)

-But I mean, Belsnickel? Who wouldn’t want to spend the holiday with HIM?

-So, after you eat the traditional German feast Dwight prepared for you, he reads you some old Christmas folklore while you snuggle up with Mose

-(Mose is basically a small child don’t challenge me on that.)

-The gifts are a little... unconventional, but Dwight thinks they’ll be useful

-like, he gets you guys a matching set of walkie talkies and you get him something sweet and meaningful like a framed picture of the two of you or maybe even one with Mose

-Either way, you both love the gifts and you love each other even more

 

** Michael Scott **

-Ok he loves you

-He LOVES you LOVES you

-So this boys gonna get in some serious debt just to get you a gift and he won’t even care

-You get him something sweet and small because you know neither of you have that much money

-But he goes out and gets you some really expensive jewelry 

-Because he wants to make sure you know he loves you and if that means he ends up broke, he won’t mind. 

 

** Jim Halpert **

-King of sentimentality!

-He adores you

-And he shows you that by getting you some kind of little trinket to remind you of him or something you’ve done together

-Orrrrr maybe he’ll get you some huge mega surprise gift that you’ll completely love

-like a cute little trip to New York for a weekend in which he spoiLS you to no end

-No matter what, he is the best, and snuggling up with him on Christmas eve is better than any gift he’s gonna give you

 

** Ryan Howard **

-He doesn’t have much money

-And he feels so bad about it

-Because he’s also not very good at the whole ‘being vulnerable with your emotions’ thing and getting you a cute and thoughtful gift to show how much he loves you

-So, he asks his mom

-And she helps him put together some sweet, inexpensive thing- like a photo album or something

-He really does love you but sometimes he needs a little help figuring out how to show it

-But you’d LOVE it and the fact that he asked his mom for help? adorable. 

-And maybe he actually cuddled with you this time

-Not because he wanted to

-But because it was a special occasion

-or so he says....

 

** Toby Flenderson **

-His favorite thing is seeing you with Sasha

-So, when he gets to spend Christmas with BOTH of you...

-Seeing how happy you both are together brings him more joy than anything

-And when he’s out shopping for your gift it’s so hard for him to not just get you an engagement ring even if he knows it’s too soon and he’s so scared you’ll say no

-because GOD you would be such a good mother and he just wants to be with you forever

-but if he did hypothetically end up asking you... let’s just say you wouldn’t object

 

**Gabe Lewis**

-He would be so nervous about getting you a gift

-As if him getting you something you aren’t completely in love with would make you leave him

-Sometimes you wish he wouldn’t be so nervous around you

-But it also reminds you of how much he cares

-Even if he’s too scared to properly show it

-So when he tries to set up some elaborate Christmas scavenger hunt and fails completely

-you don’t really mind

-because you wouldn’t trade his awkwardness for anything

 

**Andy Bernard**

-He buys you so much stuff

-Because you deserve it

-and theres nothing he wants more than to spoil you

-So shut up and LET HIM

-because nobody could treat you better than the Narddog does

-and you couldn’t possibly love anybody more


	17. When You See THEM Cry

**Summary for the Chapter:**

> A little something to get you through that awkward phase between Christmas and New Years

** Dwight Schrute **

-He doesn’t really cry all that much

-He just does that weird moaning thing when he’s really, really down

-Except this ONE time you caught him shedding actual tears

-A moment he’ll never admit to

-When you slipped out of bed to see what was keeping him

-and found him reading  _ Harry Potter and the Deathly Hallows  _ all by himself in the dim light

-and you knew he had gotten to that  _one_ part

-So, Dwight? Shedding a few tears? Who were you to hold it against him?

-And even if the reason for his sadness wasn’t all that serious, seeing him upset like that just made you want to crawl into his lap and stay there until the book was finished

-and if he let you? If he  _loved_ having you there, so close to him? Well, that’s his business. 

 

**Michael Scott**

-Michael is really lonely

-Don’t get me wrong, having you in his life has brought him SO much joy

-But all Michael has ever wanted was a friend

-And as much as he loves spending time with you, his need to be liked is still kinda there

-So, one night, when he comes back from improv all sad, you don’t even have to ask him what happened

-You just open your arms and he climbs right into them, snuggling up against you on the sofa

-You run your hand up and down his arm for awhile

-putting on some  _Whose Line Is It Anyway?_

-and pretending you can’t here him cry

-Not minding the fact that his tears soak your pjs a little

 

**Jim Halpert**

-He doesn’t want to cry in front of you

-because he knows you both knew this would happen

-Watching  _Marley and Me_ ? Really?

-Anybody with a soul would bawl their eyes out at that movie

-So you try not to smirk when Jim tries to

maintain his composure (to no avail, of course)

-and snuggle a little closer into his chest, shamelessly wiping your own tears

 

** Ryan Howard **

-He gets so frustrated 

-Never with you

-But with himself or, of course, Michael

-Ryan truly has a soft spot for the guy, and he tries to be nice, he  _really_ does

-but sometimes it just gets to be too much and the pressure is overwhelming and the little crush he has on him wouldn’t bother him so much if Michael just wasn’t so pushy all the time

-and those are the days when he wonders if maybe he really did make the wrong decision by going to that temp agency

-and there’s this  one  time he comes to you -because you’re what makes him think going to that temp agency was the best decision he’s ever made

-and he can’t help but cry a little because he’s just so frustrated and disappointed and he just wants to feel successful already

-So  _he_ initiates the cuddling because he just needs you right now

-needs you running your fingers through his hair all gently like you do

-needs you to whisper  _ I love you  _ to him and

- _It’ll be okay, sweet boy._

 

** Toby Flenderson **

-I hate to go after Michael again

-but you KNOW he’s made Toby cry before

-(and I just can’t bring myself to write anything sad about Sasha)

-It’s after the deposition

-When he tries so hard to comfort Michael

-He can’t help but just feel  _ hurt  _ when Michael pushes his tray off the table

-because, like, Toby puts his whole heart out there

-He opens up to him, makes himself vulnerable

-and Michael thanks him by ruining his lunch

-God, if that isn’t enough to make you want to chew Michael out

-but Toby insists you don’t 

-So you spend the evening making him dinner and kissing him and reassuring him that you just love him so, so much

-and if you also plot a little revenge on Michael anyway, Toby didn’t have to know 

 

** Gabe Lewis **

-He let Jo down

-At least, that’s what he keeps telling himself 

-and once those thoughts start spiraling, it’s hard to get them to stop

-So, you come home from work to find him crying on the bathroom floor

-and he’s so embarrassed you’re seeing him like this because he’s supposed to be the one making sure you’re okay

-but you let him know that it’s more than okay for him to be this vulnerable with you

-that you’d never take advantage of him

-and he should never be embarrassed

-because no matter what he thinks about your relationship, you still think of Gabe as  _your_ baby

-your precious little angel that just deserves the world

-So, if you get a backache from holding him on the floor in front of the bathtub, you’re never gonna complain about it

 

** Andy Bernard **

-When he gets casted as Curly in  _ Oklahoma! _ , boy is he excited

-Because, like, not only is that one of his favorite musicals ever but- playing the male lead?? This is a dream come true for him

-So much so that he calls his mom

-Which you just know is going to end in disaster

-but you let him, because it’s his mom

and maybe, just  maybe  she’ll be good to him this time

-Of course, she’s not

and you’re the one who has to wipe his tears

-Who has to tell him how loved he is, even if he can’t seem to get any love from his own parents

-You hug him and let him cry on your shoulder and even sing a song or two from his favorite musical, even if you can’t sing all that well

-Just loud enough that he can hear it, a soft whisper ghosting along his ear

-because you’d do anything to make him feel better


End file.
